U.S. patent application number 10/325406 was filed with the patent office on 2003-08-14 for use of ferulic acid amides as flavor compounds.
Invention is credited to Kindel, Gunter, Krammer, Gerhard, Ley, Jakob Peter, Muche, Sylvia, Reiss, Ingo.
Application Number | 20030152682 10/325406 |
Document ID | / |
Family ID | 26010877 |
Filed Date | 2003-08-14 |
United States Patent
Application |
20030152682 |
Kind Code |
A1 |
Ley, Jakob Peter ; et
al. |
August 14, 2003 |
Use of ferulic acid amides as flavor compounds
Abstract
The present invention relates to the use of various ferulic acid
amides as pungent compounds and aroma compounds having a
heat-generating effect in preparations used in nutrition, oral
hygiene or consumed for pleasure.
Inventors: |
Ley, Jakob Peter;
(Holzminden, DE) ; Krammer, Gerhard; (Holzminden,
DE) ; Muche, Sylvia; (Holzminden, DE) ;
Kindel, Gunter; (Hoxter, DE) ; Reiss, Ingo;
(Holzminden, DE) |
Correspondence
Address: |
BAYER POLYMERS LLC
100 BAYER ROAD
PITTSBURGH
PA
15205
US
|
Family ID: |
26010877 |
Appl. No.: |
10/325406 |
Filed: |
December 20, 2002 |
Current U.S.
Class: |
426/534 |
Current CPC
Class: |
A23L 27/204
20160801 |
Class at
Publication: |
426/534 |
International
Class: |
A23L 001/22 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 27, 2001 |
DE |
10164263.6 |
May 23, 2002 |
DE |
10222883.3 |
Claims
What is claimed is:
1. A flavor compound comprising
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(-
4-hydroxy-3-methoxyphenyl)-(2E)-propenamide,
N-[2-(4-hydroxy-3-methoxyphen-
yl)-ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2Z)-propenamide,
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-prop-
anamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2-
E)-propenamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxy-ph-
enyl)-(2Z)-propenamide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxy-phen-
yl)-(2E)-propenamide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxyphenyl)-
-(2Z)-propenamide,
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-dimethoxyphenyl- )-(2
E)-propenamide and
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-dimethoxyp-
henyl)-(2Z)-propenamide or a mixture thereof.
2. The flavor compound according to of claim 1, wherein the
compound is a pungent compound or flavor compound having a
heat-generating effect.
3. Preparations for nutirtional, oral hygene or pleasure
compositions comprising
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyp-
henyl)-(2E)-propenamide,
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydro-
xy-3-methoxyphenyl)-(2Z)-propenamide,
N-[2-(4-hydroxy-3-methoxyphenyl)ethy-
l]-3-(4-hydroxy-3-methoxyphenyl)-propanamide,
N-[2-(3,4-dihydroxyphenyl)et-
hyl]-3-(4-hydroxy-3-methoxy-phenyl)-(2E)-propenamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2Z)-prope-
namide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxyphenyl)-(2E)-propenam-
ide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxyphenyl)-(2Z)-propenamide-
,
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-dimethoxyphenyl)-(2E)-propenamid-
e or
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-dimethoxyphenyl)-(2Z)-propena-
mide.
4. Preparations according to claim 3 comprising at least one
further pungent or hot-tasting substance.
5. Preparations according to claim 3 further comprising at least
one pungent-tasting plant extract.
6. Preparations according to claim 3 comprising at least one
further pungent or hot-tasting substance and at least one
pungent-tasting plant extract.
7. An alcoholic beverage preparation comprising
N-[2-(4-hydroxy-3-methoxyp-
henyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2E)-propenamide,
N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2Z-
)-propenamide,
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-metho-
xyphenyl)-propanamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-met-
hoxyphenyl)-(2E)-propenamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydrox-
y-3-methoxy-phenyl)-(2Z)-propenamide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4--
dihydroxy-phenyl)-(2E)-propenamide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-di-
hydroxyphenyl)-(2Z)-propenamide,
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-d-
imethoxyphenyl)-(2E)-propenamide and
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3-
,4-dimethoxyphenyl)-(2Z)-propenamide or a mixture thereof.
8. An odor compound comprising
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-
-hydroxy-3-methoxyphenyl)-(2E)-propenamide,
N-[2-(4-hydroxy-3-methoxypheny-
l)-ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2Z)-propenamide,
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-prop-
anamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2
E)-propenamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxy-p-
henyl)-(2Z)-propenamide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxy-phe-
nyl)-(2E)-propenamide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxyphenyl-
)-(2Z)-propenamide,
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-dimethoxypheny-
l)-(2E)-propenamide and
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-dimethoxyp-
henyl)-(2Z)-propenamide or a mixture thereof.
9. A seasoning mixture comprising
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-
-(4-hydroxy-3-methoxyphenyl)-(2E)-propenamide,
N-[2-(4-hydroxy-3-methoxyph-
enyl)-ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2Z)-propenamide,
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-prop-
anamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2-
E)-propenamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxy-ph-
enyl)-(2Z)-propenamide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxy-phen-
yl)-(2E)-propenamide,
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxyphenyl)-
-(2Z)-propenamide,
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-dimethoxyphenyl-
)-(2E)-propenamide and
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-dimethoxyph-
enyl)-(2Z)-propenamide or a mixture thereof.
Description
FIELD OF THE INVENTION
[0001] The present invention relates to the use of
N-[2-(4-hydroxy-3-metho-
xyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2E)-propenamide or
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2Z)-
-propenamide (hereinafter feruloylmethoxytyramines for short),
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-prop-
anamide (hereinafter dihydroferuloylmethoxytyramine for short),
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2E)-prope-
namide or
N-[2-(3,4-Dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(-
2Z)-propenamide (hereinafter feruloyldopamines for short),
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxyphenyl)-(2
E)-propenamide or
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxyphenyl)-(2Z)-propenamide
(hereinafter caffeoyltyramines for short) and
N-[2-(3,4-dimethoxyphenyl)e-
thyl]-3-(3,4-dimethoxyphenyl)-(2E)-propenamide or
N-[2-(3,4-dimethoxypheny-
l)ethyl]-3-(3,4-dimethoxyphenyl)-(2Z)-propenamide (hereinafter
rubenamines for short) as flavor compounds, such as pungent
principles and flavor compounds having a heat-generating effect in
preparations used in nutrition, oral hygiene or consumed for
enjoyment. In addition, the present invention relates to
preparations used in nutrition, oral hygiene or consumed for
pleasure which contain the ferulic acid amides of the present
invention, and to processes for preparing the novel
preparations.
BACKGROUND OF THE INVENTION
[0002] Capsaicin
[N-(4-hydroxy-3-methoxybenzyl)-8-methyl-(6E)-nonenamide] and other
capsaicinoids have been known since as long as 1871 as hot-tasting
and heat-generating flavor compounds from various Capsicum species,
in particular chilli. At an appropriately low dose of the
capsaicinoids (the threshold is at a dilution of approximately
1:10.sup.5), only a pleasant neutral pungency and a hot feeling in
the mouth are perceived. A problem with capsaicin is its high acute
toxicity (LD.sub.50 (mouse oral) 47 mg), which makes it difficult
to apply in preparations, and the chronic gastritis, kidney damage
and liver damage which occur with frequent use and overdose (Rompp
Lexikon Naturstoffchemie, [Rompp's dictionary of the chemistry of
natural substances], Thieme, 1997, p. 109). Thus, despite the good
sensory properties, there is a requirement for less problematic
pungent principles. Although piperine (1-piperoylpiperidine), a
constituent of white pepper, also causes a very hot impression
(Rompp Lexikon Naturstoffchemie, Thieme 1997, p. 500), compared
with capsaicin, it displays a relative pungency of only
approximately 1%. Furthermore, piperine has an intense
characteristic taste reminiscent of pepper, so that in many
preparations it can only be used with restrictions.
[0003] EINBETTEN
[0004] The literature describes some pungent principles based on
4-hydroxy-3-methoxybenzylamine (hereinafter vanillylamine).
Chemical Products, 1954, March, pp. 102-106 gives an extensive list
of substances evaluated. These include
N-(4-hydroxy-3-methoxybenzyl)-4-hydroxy-3-methox-
y-(2E)-propenamide (ferulic acid N-vanillylamide) which, in
contrast to the vanillylamides of long-chain aliphatic acids, is
not described as pungent.
[0005] Accordingly, it is an object of the present invention to
find substances having a pungent and heat-generating effect and a
neutral flavor profile which occur naturally and can be used as
flavor compounds in preparations used in nutrition, oral hygiene or
consumed for pleasure.
SUMMARY OF THE INVENTION
[0006] The present invention therefore relates to the use of
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2E)-
-propenamide (trans-feruloylmethoxytyramine),
N-[2-(4-hydroxy-3-methoxyphe-
nyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2Z)-propenamide
(cis-feruloylmethoxytyramine),
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(-
4-hydroxy-3-methoxyphenyl)-propanamide
(dihydroferuloylmethoxytyramine),
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2E)-prope-
namide (trans-feruloyldopamine),
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hyd-
roxy-3-methoxyphenyl)-(2Z)-propenamide (cis-feruloyldopamine),
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxyphenyl)-(2E)-propenamide
(trans-caffeoyltyramine),
N-[2-(4-hydroxyphenyl)ethyl]-3-(3,4-dihydroxyph-
enyl)-(2Z)-propenamide, (cis-caffeoyltyramine),
N-[2-(3,4-dimethoxyphenyl)-
ethyl]-3-(3,4-dimethoxyphenyl)-(2E)-propenamide (trans-rubenamine)
and/or
N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3,4-dimethoxyphenyl)-(2Z)-propenamide
(cis-rubenamine) as flavor compounds, preferably as pungent
principles and flavor compounds having a heat-generating effect,
more preferably as pungent principles and flavor compounds having a
heat-generating effect in preparations used in nutrition, oral
hygiene or consumed for pleasure.
[0007] The present invention further relates to preparations,
semi-manufactured products and odor, flavor and taste compositions
containing these compounds.
[0008] EINBETTENTrans-Feruloylmethoxytyramine (CAS No. 78510-19-7)
has already been described, for example, in Agric. Biol. Chem.,
1984, 48 (6), 1653-1654 as a constituent of sugarbeet seeds.
According to Nat. Med., 1994, 48 (4), 304-306, feruloyldopamine has
been found in Atraphaxis spinosa L., var. sinaica Boiss.
cis-Feruloylmethoxytyramine (CAS No. 219773-49-6) has been found in
the seeds of an onion species (Allium tuberosum) (Zhongcaoyao,
2000, 31 (4), pp. 244 ff.; Chemical Abstracts 2000, Vol. 133,
263831). JP 2000 129,257 describes the use of
trans-feruloyl-methoxytyramine and trans-feruloyldopamine as
antioxidants for therapeutic applications. trans-Caffeolytyramine
has been found, for example, in onion species (Biosci. Biotech.
Biochem. Vol. 61,1997, Issue 7, pages 1138-1141). Trans-Rubenamine
has been found in Zanthoxylum species (Phytochemistry Vol. 28,
1989, pp. 839ff.).
[0009] In the literature, the use as flavor compounds, in
particular the use as pungent and hot-tasting flavor compounds, is
not described.
[0010] Surprisingly, the inventive ferulic acid amides show a
pleasantly pungent and hot taste impression, which is neutral and
persists for a relatively long time in sensory testing.
BRIEF DESCRIPTION OF THE DRAWINGS
[0011] FIG. 1 illustrates the chemical formulae of 1: capsaicin, 2:
piperine, 3: ferulic acid N-vanillylamide. In the formulae, Me is
methyl.
[0012] FIG. 2 illustrates the chemical formulae of 4:
trans-feruloyl-methoxytyramine, 5: cis-feruloylmethoxytyramine, 6:
dihydroferuloylmethoxytyramine, 7: trans-feruloyidopamine, 8:
cis-feruloyldopamine, 9: trans-caffeoyltyramine, 10:
cis-caffeoyltyramine, 11: trans-rubenamine, 12: cis-rubenamine. In
the formulae, Me is methyl.
DETAILED DESCRIPTION OF THE INVENTION
[0013] The various ferulic acid amides, their stereoisomers and
salts can be used according to the present invention in each case
alone or as mixtures.
[0014] The salts of the ferulic acid amides can be monovalent or if
appropriate polyvalent phenolate salts with inorganic cations.
Preference is given to the cations of lithium, sodium, potassium,
the ammonium ion, the cations of magnesium, calcium and strontium,
or the cations of aluminum, zinc, copper, iron or manganese.
[0015] Preferably, the ferulic acid amides of the present invention
are used in combination with other pungent and/or hot-tasting
substances or hot-tasting plant extracts. In this manner, a rounded
sensory profile can be achieved. Preferably, the combination of one
or more of the ferulic acid amides with an extract of pepper, water
pepper, chilli, extract of grains of paradise or ginger in a weight
ratio of 0.01:1 to 100:1, preferably 0.1:1 to 10:1, produces a
pleasant sensory profile.
[0016] Other pungent and/or hot-tasting substances can be, for
example, capsaicin, dihydrocapsaicin, gingerol, paradol, shogaol,
piperine, carboxylic acid N-vanillylamides, preferably nonanoic
acid N-vanillylamide, 2-alkenamides, in particular 2-nonenoic acid
N-isobutylamide, pellitorine or spilanthol, 2-nonenoic acid
N-4-hydroxy-3-methoxyphenylamide, alkyl ethers of
4-hydroxy-3-methoxybenz- yl alcohol, in particular
4-hydroxy-3-methoxybenzyl n-butyl ether, alkyl ethers of
3-hydroxy-4-methoxybenzyl alcohol, alkyl ethers of
3,4-dimethoxybenzyl alcohol, alkyl ethers of
3-ethoxy-4-hydroxybenzyl alcohol, alkyl ethers of
3,4-methylenedioxybenzyl alcohol, nicotinaldehyde, methyl
nicotinate, propyl nicotinate, 2-butoxyethyl nicotinate, benzyl
nicotinate, 1-acetoxychavicol, polygodial or iso-drimeninol.
[0017] Pungent-tasting plant extracts can be all plant extracts
suitable for nutrition which cause a pungent or hot sensory
impression. Preferred pungent-tasting plant extracts are, for
example, pepper extract (Piper ssp., preferably Piper nigrum),
water pepper extract (Polygonum ssp., preferably Polygonum
hydropiper), extracts of Allium ssp. (preferably onion and garlic
extract), extracts of radish (Raphanus ssp.), horse radish extracts
(Cochlearia armoracia), extracts of black (Brassica nigra), wild or
yellow mustard (Sinapis ssp., preferably Sinapis arvensis and
Sinapis alba), pellietory root extracts (Anacyclus ssp., in
particular Anacyclus pyrethrum L.), cone flower extracts
(Echinaceae ssp.), extracts of Szechwan pepper (Zanthoxylum ssp.,
in particular Zanthoxylum piperitum), Spilanthese extract
(Spilanthes ssp., preferably Spilanthes acmella), chilli extract
(Capsicum ssp., in particular Capsicum frutescens), grain of
paradise extract (Aframomum ssp., preferably Aframomum melegueta
[Rose] K. Schum.), ginger extract (Zingiber ssp., preferably
Zingiber officinale) and galanga extract (Kaempferia galanga or
Alpinia galanga).
[0018] The pungent-tasting plant extracts can be obtained from the
corresponding fresh or dried plants or plant parts, preferably from
white, green or black peppercorns, water peppercorns, onions and
garlic, radish root, horse radish, mustard seed, cone flower root,
pellitory root, plant parts from Zanthoxylum species, plant parts
of spilanthes species, chilli peppers, grains of paradise or ginger
or galanga roots, by extracting the dried plant parts, preferably
comminuted in advance, with a solvent suitable for food and drink,
but preferably ethanol, water, hexane or heptane, or ethanol/water
mixtures, at 0.degree. C. up to the boiling point of the respective
solvent or mixture, then filtering and completely or partially
concentrating the filtrate, preferably by distillation or
spray-drying. The resultant crude extract can then be worked up
further, for example it can be treated with steam at pressures from
0.01 mbar to atmospheric pressure and/or taken up in a solvent
suitable for food and drink.
[0019] A solvent suitable for food and drink can be, for example,
water, ethanol, methanol, propylene glycol, glycerol, acetone,
dichloromethane, diethyl ether, hexane, heptane or supercritical
carbon dioxide or mixtures of the above-mentioned solvents.
[0020] It has also proved to be advantageous that the ferulic acid
amides of the present invention, preferably the ferulic acid amides
in combination with pungent-tasting plant extracts, can imitate the
pungent taste of alcohol in alcoholic beverages or preparations of
alcoholic beverages and it is thus possible to make the alcohol
content lower in alcoholic beverages or in preparations of
alcoholic beverages while maintaining the sensory rating.
[0021] The present invention further relates to preparations used
in nutrition, oral hygiene or consumed for pleasure containing
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-(2E)-
-propenamide,
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hydroxy-3-methox-
yphenyl)-(2Z)-propenamide,
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3-(4-hyd-
roxy-3-methoxyphenyl)-propanamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-h-
ydroxy-3-methoxyphenyl)-(2E)-propenamide,
N-[2-(3,4-dihydroxyphenyl)ethyl]-
-3-(4-hydroxy-3-methoxyphenyl)-(2Z)-propenamide,
N-[2-(4-hydroxyphenyl)eth-
yl]-3-(3,4-dihydroxyphenyl)-(2E)-propenamide,
N-[2-(4-hydroxyphenyl)ethyl]-
-3-(3,4-dihydroxyphenyl)-(2Z)-propenamide,
N-[2-(3,4-dimethoxyphenyl)ethyl-
]-3-(3,4-dimethoxyphenyl)-(2E)-propenamide and/or
N-[2-(3,4-dimethoxypheny-
l)ethyl]-3-(3,4-dimethoxyphenyl)-(2Z)-propenamide.
[0022] The preparations of the present invention consumed for
nutrition or pleasure contain the ferulic acid amides in an active
amount and optionally other constituents. They generally contain
0.000001% to 10% by weight, preferably 0.0001 to 1% by weight, more
preferably 0.0001% by weight to 0.1% by weight, based on the total
weight of the preparation, of the ferulic acid amides or mixtures
thereof. Other conventional base materials, aids and additives for
foods or drinks can be present at amounts of 5 to 99.999999% by
weight, preferably 10 to 80% by weight, based on the total weight
of the preparation. In addition, the preparations can contain water
at an amount of up to 99.999999% by weight, preferably 5 to 80% by
weight, based on the total weight of the preparation.
[0023] The preparations consumed for nutrition or pleasure in the
context of the present invention are, for example, bakery products
(for example bread, dry biscuits, cakes, other baked goods),
confectionery (for example types of chocolate, chocolates, sweets,
hard and soft caramels, chewing gum), alcoholic or nonalcoholic
beverages (for example coffee, tea, wine, wine-containing
beverages, beer, beer-containing beverages, liqueurs, schnapps,
wine brandies, fruit-containing lemonades, isotonic drinks,
refreshments, nectars, fruit and vegetable juices, fruit juice or
vegetable juice preparations), instant drinks, meat products (for
example ham, fresh sausage preparations or uncooked sausage
preparations), eggs or egg products (dried egg, egg white, egg
yolk), cereal products (for example breakfast cereals, meusli
bars), milk products (for example milk drinks, dairy ice cream,
yogurt, kefir, fresh cheese, soft cheese, hard cheese, dried milk
powder, butter, buttermilk, whey), fruit preparations (for example
jams, marmalades, fruit ices, fruit sauces), vegetable preparations
(for example ketchup, sauces, dried vegetables), snacks (for
example baked or deep-fried potato crisps or potato dough products,
maize- or peanut-based extrudates), fat- and oil-based products or
emulsions thereof (for example mayonnaise, remoulade, dressings),
prepared dishes and soups, spices, seasoning mixes and, preferably
seasonings for sprinkling, which are used in the snacks sector. The
preparations in the context of the present invention can also be
used as semi-manufactured products for the production of further
preparations consumed for nutrition or pleasure. The preparations
in the context of the present invention can also be food
supplements in the form of capsules, tablets (uncoated or coated
tablets, for example coatings resistant to gastric juice), dragees,
granules, pellets, solids mixtures, dispersions in liquid phases,
as emulsions, as powders, as solutions, as pastes or as other
swallowable or chewable preparations.
[0024] The present invention also relates to preparations used for
oral hygiene, preferably as dental care compositions such as
toothpastes, tooth gels, toothpowders, mouthwashes, chewing gums
and other oral care compositions containing the ferulic acid amides
in an active amount with or without other customary base materials,
aids and additives for such preparations. They generally contain
0.000001% by weight to 10% by weight, preferably 0.0001 to 1% by
weight, more preferably 0.0001% by weight to 0.1% by weight, based
on the total weight of the preparation, of the ferulic acid amides
or mixtures thereof. Other customary base materials, aids and
additives for preparations used for oral hygiene can be present at
amounts of 0.000001 to 99.999999% by weight, preferably 10 to 80%
by weight, based on the total weight of the preparation. In
addition, the preparations can contain water in an amount up to
99.999999% by weight, preferably 5 to 80% by weight, based on the
total weight of the preparation.
[0025] Dental care compositions containing the ferulic acid amides
according to the present invention generally contain an abrasive
system (abrasive or polishes) for example silicic acids, calcium
carbonates, calcium phosphates, aluminum oxides and/or
hydroxylapatites, of surface active substances, for example sodium
lauryl sulphate, sodium lauryl sarcosinate and/or
cocamidopropylbetaine, of humectants, for example glycerol and/or
sorbitol, of thickeners, for example carboxymethylcellulose,
polyethylene glycols, carrageenans and/or Laponites.RTM., of
sweeteners, for example saccharin, of stabilizers and of active
compounds, for example sodium fluoride, sodium monofluorophosphate,
tin difluoride, quaternary ammonium compounds, zinc citrate, zinc
sulphate, tin pyrophosphate, tin dichloride, mixtures of various
pyrophosphates, triclosan, cetylpyridinium chloride, aluminum
lactate, potassium citrate, potassium nitrate, potassium chloride,
strontium chloride, hydrogen peroxide, flavors and/or sodium
bicarbonate.
[0026] Chewing gums containing the ferulic acid amides of the
present invention generally contain a chewing gum base, that is to
say a gum base becoming plastic during chewing, of sugars of
various types, sugar substitutes, sweeteners, sugar alcohols,
humectants, thickeners, emulsifiers, stabilizers and flavors.
[0027] The preparations containing the ferulic acid amides of the
present invention can be prepared in such a manner that the ferulic
acid amides are incorporated as the substance alone, as a solution
or in the form of a mixture with a solid or liquid carrier into the
preparations consumed for nutrition or pleasure.
[0028] To produce the preparations, the ferulic acid amides and if
appropriate, other constituents of the preparation of the present
invention can also be incorporated in advance into emulsions, into
liposomes, for example starting from phosphatidyl choline, into
microspheres, into nanospheres or else into capsules made of a
matrix suitable for food and drinks, for example of starch, starch
derivatives, other polysaccharides, natural fats, natural waxes or
proteins, for example gelatin. The ferulic acid amides can be
complexed in advance with suitable complexing agents, for example
with cyclodextrins or cyclodextrin derivatives, preferably
1-cyclodextrin, and used in this form.
[0029] Further constituents which can be used for the preparations
of the present invention consumed for nutrition or pleasure are
customary base materials, aids and additives for foods and drinks,
for example water, mixtures of fresh or processed, plant or animal
base materials or raw materials (for example raw, fried, dried,
fermented, smoked and/or cooked meat, egg, bones, cartilage, fish,
vegetables, fruits, herbs, nuts, vegetable or fruit juices or
pastes or mixtures thereof), digestible or indigestible
carbohydrates (for example sucrose, maltose, fructose, glucose,
dextrins, amylose, amylopectin, inulin, xylans, cellulose), sugar
alcohols (for example sorbitol), natural or hardened fats (for
example tallow, lard, palm kernel fat, coconut fat, hardened
vegetable fat), oils (for example sunflower seed oil, peanut oil,
maize germ oil, olive oil, thistle oil, fish oil, soybean oil,
sesame seed oil), fatty acids or their salts (for example potassium
stearate), proteinogenic or nonproteinogenic amino acids and
related compounds (for example taurine, creatine, creatinine),
peptides, native or processed proteins (for example gelatin),
enzymes (for example peptidases, glycosidases, lipases), nucleic
acids, nucleotides, taste-modulating substances (for example sodium
glutamate, 2-phenoxy-propionic acid, hydroxyflavanones),
emulsifiers (for example lecithins, diacylglycerols), stabilizers
(for example carageenan, alginate), preservatives (for example
benzoic acid, sorbic acid), antioxidants (for example tocopherol,
ascorbic acid), chelators (for example citric acid), organic or
inorganic acidulants (for example malic acid, acetic acid, citric
acid, tartaric acid, phosphoric acid), additional bitter substances
(for example quinine, caffeine, limonin), sweeteners (for example
saccharin, cyclamate, aspartame, neotame, neohesperidine
dihydrochalcone, sucralose), mineral salts (for example sodium
chloride, potassium chloride, magnesium chloride, sodium
phosphates), substances inhibiting enzymatic browning (for example
sulphite, ascorbic acid), essential oils, plant extracts, natural
or synthetic colours or colour pigments (for example carotenoids,
flavonoids, anthocyans, chlorophyll and derivatives thereof),
spices, and odour compounds, synthetic, natural or nature-identical
flavor and taste compounds.
[0030] Preferably, the inventive preparations can also contain a
flavor composition in order to round off and refine the taste
and/or odor of the preparation. Suitable flavor compositions
contain, for example, synthetic, natural or nature-identical flavor
compounds and odor compounds, preferably other pungent or
hot-tasting substances.
[0031] The present invention further relates to the use of the
preparations as semi-manufactured products for flavoring
preparations fabricated therefrom as finished goods.
[0032] The present invention further relates to the use of the
preparations as odor, flavor or taste composition or as a seasoning
mixture.
EXAMPLES
Example 1
Tasting the Pungent Compounds Trans-feruloyl-methoxytyramine,
Cis-feruloylmethoxytyramine, Trans-caffeoyltyramine,
Trans-rubenamine and Piperine
[0033] The substance, under test, was dissolved in ethanol and the
ethanolic solution was then diluted with an 11% strength by weight
sugar solution (final concentration: c). For tasting, in each case
approximately 5 ml of the sugar solution was swallowed. If the
threshold value of the substance was known, a value just above the
threshold value is chosen for the tasting. A group of 8 testers
tasted the solutions.
[0034] Profile of Trans-feruloylmethoxytyramine:
[0035] c=10 ppm: body, sweet, heat develops after delay,
long-lasting, especially in the pharyngeal cavity (in the case of 4
participants), adherent, slightly anaesthetizing action
[0036] c=20 ppm: sweet, aniseed-like, benzaldehyde, heat develops
after a delay (in the case of 8 participants), long-lasting,
especially in the pharyngeal cavity, pleasant pepper pungency
[0037] Profile of Cis-feruloylmethoxytyramine:
[0038] c=1 ppm: pungency builds up slowly.
[0039] Profile of Trans-caffeoyltyramine:
[0040] c=1 ppm: pungency occurs after a delay, anaesthetizing
pungency.
[0041] Profile of Trans-rubenamine:
[0042] c=1 ppm: pleasant mild pungency, builds up slowly.
[0043] Comparative Test
[0044] Profile of Piperine:
[0045] c=500 ppb: weak development of heat after a long delay (in
the case of 6 participants), neutral pungency occurring after a
delay (in the case of 6 participants)
[0046] c=20 ppm: weak development of heat after a long delay (in
the case of 8 participants), sharp, burning, persistent,
peppercorn, in the entire oral region (in the case of 8
participants)
Example 2
Use of Trans-feruloylmethoxytyramine in Liqueur Beverages as
Sensory Alcohol Substitute
[0047] The grains of paradise extract used below was prepared by
stirring 800 g of ground grains of paradise with 4 kg of ethanol
(96% by volume). After filtration the filtrate was concentrated to
40 g and treated with steam at 100.degree. C. and 300 mbar. The
extract was made up to 80 g with ethanol (96% by volume).
[0048] As commercially conventional model systems, a liqueur base
of 10% by volume and a liqueur base of 5.5% by volume were
selected. The composition is shown in Tables 1 and 2.
1TABLE 1 Model system A; liqueur base 10% by volume Amount used in
% by weight Ethanol absolute, food quality 7.39% Invert sugar syrup
66.5% (dry matter) 20.00% Mains water 72.61% Total 100.00%
[0049]
2TABLE 2 Model system B; liqueur base 5.5% by volume Amount used in
% by weight Ethanol absolute, food quality 4.06% Invert sugar syrup
66.5% (dry matter) 20.00% Mains water 75.94% Total 100.00%
[0050] To the model system A were then added the solution of the
extract of grains of paradise (1% by weight in ethanol (EtOH)) at
concentrations of 1 to 3% by weight, based on the total weight of
the model system, and a solution of trans-feruloylmethoxytyramine
(1% by weight in ethanol) at a concentration of 1% by weight, based
on the total weight of the model system. Using a taste-testing
group of 8 people, the effect of grains of paradise extract
addition and trans-feruloylmethoxytyramine addition on the sensory
profile were then tested. The sensory assessment was made on a
scale of 1 (weak) to 5 (strong). The results are shown in Table
3.
3TABLE 3 Sensory assessment of the pungency of a liqueur base with
addition of grains of paradise extract and
trans-feruloylmethoxytyramine Pungency Addition to model system
(median), A Scale 1-5 Sensory description 1% by weight grains of
1.5 Weak effect, slight vanilla paradise extract solution note,
slightly pungent (1% by weight in EtOH) 2% by weight grains of 3.25
Readily identifiable, good, paradise extract solution correct
effect, too pungent, (1% by weight in EtOH) sweet, vanilla,
unpleasant aftertaste, very vigorous 3% by weight grains of 5 Too
pungent, too strong, paradise extract solution burning, biting
aftertaste (1% by weight in EtOH) (ginger), very clinging 1% by
weight trans- 2 Sweet, vanilla, fruity, less
feruloylmethoxytyramine bitter, correct effect, slight solution
pungency in the impact, alter (1% by weight in EtOH) 10 sec
vigorous pungency, pleasant, little pungency in aftertaste, not
very clinging
[0051] Then, to model system A the solution of a grains of paradise
extract (10% by weight in ethanol) was added at concentrations of
0.1 to 0.2% by weight, based on the total weight of the model
system, and a solution of trans-feruloylmethoxytyramine (10% by
weight in ethanol) at a concentration of 0.01 to 0.02% by weight,
based on the total weight of the model system. Using a
taste-testing group of 8 people, again the effect of grains of
paradise extract addition and of trans-feruloylmethoxytyramine
addition on the sensory profile were tested. In addition, the
combined action was tested. The results are shown in Table 4.
4TABLE 4 Test of the combined action of grains of paradise extract
and trans- feruloylmethoxytyramine. Addition to model system A
Comments 0.015% by weight grains of paradise Strong, good effect,
sharp extract solution (10% by weight in EtOH) alcoholic pungency
0.02% by weight trans- Mild, pungency very similar
feruloylmethoxytyramine solution to alcoholic pungency (10% by
weight EtOH) 0.01% by weight grains of paradise Very mild, slight
pungency extract solution (10% by weight in EtOH) and 0.01% by
weight trans- feruloylmethoxytyramine solution (10% by weight in
EtOH) 0.01% by weight grains of paradise Profile similar to
alcoholic extract solution (10% by weight in EtOH) pungency, very
mild and 0.02% by weight trans- feruloylmethoxytyramine solution
(10% by weight in EtOH) 0.015% by weight grains of paradise Marked
pungency, strong, extract solution (10% by weight in EtOH) similar
to alcoholic pungency and 0.015% by weight trans-
feruloylmethoxytyramine solution (10% by weight in EtOH)
[0052] After the individual testing and the combined testing
clearly showed the effect of alcoholic pungency, a direct
comparison of model system A having an alcohol strength of 10% by
volume and model system B of 5.5% by volume was performed. Model
system B received an addition of grains of paradise extract
solution (10% by weight in EtOH) and trans-feruloylmethoxytyramine
solution (10% by weight in EtOH) up to the concentrations reported.
The results of the comparative testing are shown in Table 5.
5TABLE 5 Comparative testing of model system A without addition and
model system B with combined addition of grains of paradise extract
and trans- feruloylmethoxytyramine. Sensory comparison of model
system B Addition to model system B with model system A (without
addition) 0.3% by weight grains of Strong, good effect, sharp
alcoholic paradise extract solution pungency, too strong compared
with (10% by weight in EtOH) model system A 0.2% by weight grains
of Balanced, pungency very similar to paradise extract solution
alcoholic pungency in model system A (10% by weight in EtOH) 0.2%
by weight grains of Pungency, time-intensity behavior similar
paradise extract solution (10% to the alcoholic pungency in model
system by weight in EtOH) and 0.2% A by weight trans-feruloyl-
methoxytyramine (10% by weight in EtOH) 0.075% by weight grains of
Profile similar to alcoholic pungency, paradise extract solution
(10% by authentic time-intensity profile weight in EtOH) and 0.025%
compared to alcoholic pungency of model by weight trans- system A
feruloylmethoxytyramine 10% by weight in EtOH)
[0053] This use example demonstrated that alcoholic pungency can be
imitated by defined combinations of trans-feruloylmethoxytyramine
having pungent-tasting plant extracts, here, in the example, grains
of paradise extract.
Example 3
[0054] Use of Trans-feruloylmethoxytyramine in Gelled Fruits as
Flavor Intensifier
[0055] As commercially conventional model system, flavor
combinations in gelled fruits having elderberry flavor were
used:
6TABLE 6 Gelled fruits having elderberry flavor 0.07% by weight,
based on the total weight of the preparation Addition of trans-
feruloylmethoxytyramine solution (1% by weight in ethanol) Sensory
description 0.015% by weight Effect only slightly perceptible 0.03%
by weight Effect below threshold, but pleasant 0.045% by weight
Flavor fresh and rounded
Example 4
[0056] Use in an Apple Schnapps as Alcohol Intensifier
7 Sample A: 20 l Alcohol 96% by volume 5.2 l Flavor (natural apple
fruit juice liqueur flavor, 15% by volume) 27 kg Sugar syrup 1 kg
Citric acid monohydrate Make up to 100 l with de-mineralized water
Total amount 100 l
[0057]
8 Sample B: 14.90 l Alcohol 96% by volume 5.2 l Flavor (natural
apple fruit juice liqueur flavor, 15% by volume, contains 0.01% by
weight trans-feruloylmethoxy- tyramine) 27 kg Sugar syrup 1 kg
Citric acid monohydrate Make up to 100 l with de-mineralized water
Total amount 100 l
[0058] Sensory assessment Sample A: medium alcoholic pungency
[0059] Sensory assessment Sample B: medium alcoholic pungency,
further pungency identifiable
9 Amount used in Component Constituent % by weight A Demineralized
water 22.00 Sorbitol (70%) 45.00 Solbrol .RTM. M, sodium salt
(Bayer AG, 0.15 p-hydroxybenzoic acid alkylester)
Trisodiumphosphate 0.10 Saccharin, 450 fold 0.20 Sodium
monofluorophosphate 1.12 Polyethylene glycol 1500 5.00 B Sident 9
(abrasive silicon dioxide) 10.00 Sident 22 S (thickening silicon
dioxide) 8.00 Sodium carboxymethylcellulose 0.90 Titanium dioxide
0.50 C Demineralized water 4.53 Sodium lauryl sulphate 1.50 D
Flavor containing 0.1% trans- 1 feruloylmethoxytyramine
[0060] The constituents of components A and B are premixed for each
component separately and stirred well together under vacuum for 30
min at 25-30.degree. C. Component C is premixed and added to A and
B; D is added and the mixture is stirred thoroughly under vacuum at
25-30.degree. C. for 30 min. After release of vacuum, the
toothpaste is finished and can be packaged.
Example 6
[0061] Use in a Sugar-Free Chewing Gum as Flavor
10 Amount used in % Component Constituent by weight A Chewing gum
base, Company "Jagum T" 30.00 B Sorbitol, pulverized 39.00 Isomalt
.RTM. (Palatinit GmbH) 9.50 Xylitol 2.00 Mannitol 3.00 Aspartame
0.10 Acesulfame-K 0.10 Emulgum .RTM. (Colloides Naturels, Inc.)
0.30 C Sorbitol, 70% 14.00 Glycerol 1.00 D Flavor containing 0.1%
trans- 1 feruloylmethoxytyramine
[0062] Components A to D are mixed and kneaded intensively. The raw
mass can be processed, for example, in the form of thin strips, to
give ready-to-eat chewing gums.
Example 7
[0063] Use in a Mouthwash as Flavor
11 Amount used in % Component Constituent by weight A Ethanol 10.00
Cremophor .RTM. CO 40 (BASF, Detergent) 1.00 Benzoic acid 0.12
Flavor containing 0.4 % trans- 0.25 feruloylmethoxy-tyramine B
Demineralized water 83.46 Sorbitol, 70% 5.00 Sodium saccharin 450
0.07 L-Blue 5000 e.c., 1% in water (dye) 0.10
[0064] The constituents of components A and B are each mixed
separately. Component B is slowly stirred in component A until the
mixture is homogeneous.
[0065] Although the invention has been described in detail in the
foregoing for the purpose of illustration, it is to be understood
that such detail is solely for that purpose and that variations can
be made therein by those skilled in the art without departing from
the spirit and scope of the invention except as it may be limited
by the claims.
* * * * *